Lipase‐Catalyzed Synthesis of Substituted Phenylacetamides: Hammett Analysis and Computational Study of the Enzymatic Aminolysis

Liñares, Guadalupe Eugenia Garcia; Máñez, Pau Arroyo; Baldessari, Alicia

doi:10.1002/ejoc.201402749

Cited by 14 publications

(13 citation statements)

References 64 publications

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“…Some of the noteworthy pharmaceutical applications include peptide syntheses that contain usual and unusual amino acids produced by porcine pancreatic lipase and C. cylindracea lipase . Other examples are the synthesis of β‐amino acid esters, which are the chief components in many drugs, the synthesis of drugs such as milnacipran that help in clinical treatment of fibromyalgia, and the synthesis of potential anti‐malarial drugs as well as hormone receptors . The widespread usage of this reaction in the pharma domain is due to its potential in effective kinetic resolution of molecules .…”

Section: Lipase‐catalyzed Reactionsmentioning

confidence: 99%

“…Other examples are the synthesis of β‐amino acid esters, which are the chief components in many drugs, the synthesis of drugs such as milnacipran that help in clinical treatment of fibromyalgia, and the synthesis of potential anti‐malarial drugs as well as hormone receptors . The widespread usage of this reaction in the pharma domain is due to its potential in effective kinetic resolution of molecules . Other application domains of lipase‐catalyzed aminolysis include cosmetics, and agrochemical products …”

Section: Lipase‐catalyzed Reactionsmentioning

confidence: 99%

“…204 The widespread usage of this reaction in the pharma domain is due to its potential in effective kinetic resolution of molecules. 203 Other application domains of lipase-catalyzed aminolysis include cosmetics, and agrochemical products. 205…”

Section: Aminolysismentioning

confidence: 99%

See 2 more Smart Citations

Recent advances on sources and industrial applications of lipases

Sarmah

Revathi

Sheelu

et al. 2017

Biotechnology Progress

302

148

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Lipases are the industrially important biocatalysts, which are envisioned to have tremendous applications in the manufacture of a wide range of products. Their unique properties such as better stability, selectivity and substrate specificity position them as the most expansively used industrial enzymes. The research on production and applications of lipases is ever growing and there exists a need to have a latest review on the research findings of lipases. The present review aims at giving the latest and broadest overall picture of research and development on lipases by including the current studies and progressions not only in the diverse industrial application fields of lipases, but also with regard to its structure, classification and sources. Also, a special emphasis has been made on the aspects such as process optimization, modeling, and design that are very critical for further scale-up and industrial implementation. The detailed tabulations provided in each section, which are prepared by the exhaustive review of current literature covering the various aspects of lipase including its production and applications along with example case studies, will serve as the comprehensive source of current advancements in lipase research. This review will be very useful for the researchers from both industry as well as academia in promoting lipolysis as the most promising approaches to intensified, greener and sustainable processes. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 34:5-28, 2018.

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Section: Lipase‐catalyzed Reactionsmentioning

confidence: 99%

Section: Lipase‐catalyzed Reactionsmentioning

confidence: 99%

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Recent advances on sources and industrial applications of lipases

Sarmah

Revathi

Sheelu

et al. 2017

Biotechnology Progress

302

148

View full text Add to dashboard Cite

show abstract

“…[21][22][23][24][25]. In our laboratory several studies have been accomplished on the use of lipases, obtaining a wide variety of biologically active compounds, many of them new [26][27][28][29][30][31][32][33][34][35].…”

Section: Scheme 1 Structure Of Important Bile Acidsmentioning

confidence: 99%

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

et al. 2018

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In this work we present an efficient, environmentally friendly approach to the synthesis of a series of hyodeoxycholic acid derivatives applying Biocatalysis. Fifteen acetyl and ester derivatives, twelve of them new, were obtained through an enzymatic strategy in a fully regioselective way and in very good to excellent yield. In order to find the optimal reaction conditions, the influence of several parameters such as enzyme source, alcohol or acylating agent:substrate ratio, enzyme:substrate ratio, temperature and reaction solvent was considered. The excellent results obtained made this procedure very efficient, particularly considering the low amount of enzyme required. In addition, this methodology uses mild reaction conditions and has reduced environmental impact, making biocatalysis a suitable way to obtaining these bile acids derivatives.

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“…Among the enzymes, lipase (EC 3.1.1.3) was often applied for the esterification and amidation reactions (Kirchner et al, 1985;Martinek and Semenov, 2002;Vicente, 2002;Slotema et al, 2003;Tan, 2010). Due to the excellent regio-selectivity, high efficiency and environment amity, many works about lipase, especially commercial lipase Novozym 435, synthesizing high value-added amide products, applied for drug intermediates and cosmetic materials have been reported (Levinson et al, 2005;Martínková et al, 2008;Baum et al, 2011;Schwab et al, 2013;Stavila et al, 2013;Liñares et al, 2014). Among all the researches, amino alcohols have two active hydrogen groups, the amidation reaction on which have been well studied (Syrén et al, 2012;Wang et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Optimization of the Lipase-Catalyzed Selective Amidation of Phenylglycinol

Sun

Nie

Wang

et al. 2020

Front. Bioeng. Biotechnol.

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Ceramides and their analogs have a regulatory effect on inflammatory cytokines expression. It was found that a kind of ceramides analog synthesized from phenylglycinol could inhibit the production of cytokine TNF-α. However, two active hydrogen groups are present in the phenylglycinol molecule. It is difficult to control the process without hydroxyl group protection to dominantly produce amide in the traditional chemical synthesis. A selective catalytic the amidation route of phenylglycinol by lipases was investigated in this research. The results indicated that the commercial immobilized lipase Novozym 435 has the best regio-selectivity on the amide group. Based on the experimental results and in silico simulation, it was found that the mechanism of specific N-acyl selectivity of lipase was not only from intramolecular migration and proton shuttle mechanism, but also from the special structure of active site of enzyme. The optimal reaction yield of aromatic amide compound in a solvent-free system with lipase loading of 15 wt% (to the weight of total substrate) reached 89.41 ± 2.8% with very few of byproducts detected (0.21 ± 0.1% ester and 0.64 ± 0.2% diacetylated compound). Compare to other reported works, this work have the advantages such as low enzyme loading, solvent free, and high N-acylation selectivity. Meanwhile, this Novozym 435 lipase based synthesis method has an excellent regio-selectivity on most kinds of amino alcohol compounds. Compared to the chemical method, the enzymatic synthesis exhibited high regio-selectivity, and conversion rates. The method could be a promising alternative strategy for the synthesis of aromatic alkanolamides.

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Lipase‐Catalyzed Synthesis of Substituted Phenylacetamides: Hammett Analysis and Computational Study of the Enzymatic Aminolysis

Cited by 14 publications

References 64 publications

Recent advances on sources and industrial applications of lipases

Recent advances on sources and industrial applications of lipases

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

Optimization of the Lipase-Catalyzed Selective Amidation of Phenylglycinol

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